From 5b1e1239fdcdbdcf4d8aa3a522e02bd6d95fdd30 Mon Sep 17 00:00:00 2001
From: dotta <dotta@example.com>
Date: Fri, 20 Mar 2026 08:58:24 -0500
Subject: [PATCH] Fix routine run assignment wakeups

Co-Authored-By: Paperclip <noreply@paperclip.ing>
---
 server/src/__tests__/routines-service.test.ts | 37 +++++++++++++++++--
 server/src/routes/issues.ts                   |  2 +-
 .../src/services/issue-assignment-wakeup.ts   |  2 +-
 server/src/services/routines.ts               |  3 +-
 4 files changed, 37 insertions(+), 7 deletions(-)

diff --git a/server/src/__tests__/routines-service.test.ts b/server/src/__tests__/routines-service.test.ts
index 9240dfbf..2d07d63a 100644
--- a/server/src/__tests__/routines-service.test.ts
+++ b/server/src/__tests__/routines-service.test.ts
@@ -115,7 +115,20 @@ describe("routine service live-execution coalescing", () => {
     }
   });
 
-  async function seedFixture() {
+  async function seedFixture(opts?: {
+    wakeup?: (
+      agentId: string,
+      wakeupOpts: {
+        source?: string;
+        triggerDetail?: string;
+        reason?: string | null;
+        payload?: Record<string, unknown> | null;
+        requestedByActorType?: "user" | "agent" | "system";
+        requestedByActorId?: string | null;
+        contextSnapshot?: Record<string, unknown>;
+      },
+    ) => Promise<unknown>;
+  }) {
     const companyId = randomUUID();
     const agentId = randomUUID();
     const projectId = randomUUID();
@@ -161,9 +174,9 @@ describe("routine service live-execution coalescing", () => {
 
     const svc = routineService(db, {
       heartbeat: {
-        wakeup: async (agentId, opts) => {
-          wakeups.push({ agentId, opts });
-          return null;
+        wakeup: async (wakeupAgentId, wakeupOpts) => {
+          wakeups.push({ agentId: wakeupAgentId, opts: wakeupOpts });
+          return opts?.wakeup ? opts.wakeup(wakeupAgentId, wakeupOpts) : null;
         },
       },
     });
@@ -258,6 +271,22 @@ describe("routine service live-execution coalescing", () => {
     ]);
   });
 
+  it("waits for the assignee wakeup to be queued before returning the routine run", async () => {
+    let wakeupResolved = false;
+    const { routine, svc } = await seedFixture({
+      wakeup: async () => {
+        await new Promise((resolve) => setTimeout(resolve, 10));
+        wakeupResolved = true;
+        return null;
+      },
+    });
+
+    const run = await svc.runRoutine(routine.id, { source: "manual" });
+
+    expect(run.status).toBe("issue_created");
+    expect(wakeupResolved).toBe(true);
+  });
+
   it("coalesces only when the existing routine issue has a live execution run", async () => {
     const { agentId, companyId, issueSvc, routine, svc } = await seedFixture();
     const previousRunId = randomUUID();
diff --git a/server/src/routes/issues.ts b/server/src/routes/issues.ts
index 4173f1a6..0e19a871 100644
--- a/server/src/routes/issues.ts
+++ b/server/src/routes/issues.ts
@@ -782,7 +782,7 @@ export function issueRoutes(db: Db, storage: StorageService) {
       details: { title: issue.title, identifier: issue.identifier },
     });
 
-    queueIssueAssignmentWakeup({
+    void queueIssueAssignmentWakeup({
       heartbeat,
       issue,
       reason: "issue_assigned",
diff --git a/server/src/services/issue-assignment-wakeup.ts b/server/src/services/issue-assignment-wakeup.ts
index aa39d0c5..96eaa982 100644
--- a/server/src/services/issue-assignment-wakeup.ts
+++ b/server/src/services/issue-assignment-wakeup.ts
@@ -29,7 +29,7 @@ export function queueIssueAssignmentWakeup(input: {
 }) {
   if (!input.issue.assigneeAgentId || input.issue.status === "backlog") return;
 
-  void input.heartbeat
+  return input.heartbeat
     .wakeup(input.issue.assigneeAgentId, {
       source: "assignment",
       triggerDetail: "system",
diff --git a/server/src/services/routines.ts b/server/src/services/routines.ts
index 0fb8436a..f0c65c4a 100644
--- a/server/src/services/routines.ts
+++ b/server/src/services/routines.ts
@@ -619,7 +619,8 @@ export function routineService(db: Db, deps: { heartbeat?: IssueAssignmentWakeup
         status: "issue_created",
         linkedIssueId: createdIssue.id,
       });
-      queueIssueAssignmentWakeup({
+      // Ensure the wake request is durably queued before reporting the routine run as created.
+      await queueIssueAssignmentWakeup({
         heartbeat,
         issue: createdIssue,
         reason: "issue_assigned",